Since the publication of her first novel, Jeanette Winterson has been acclaimed as one of the most promising writers on the English postmodern literary scene. This study takes into consideration seven works, from Oranges Are Not the Only Fruit (1985) to The PowerBook (2000) in which Winterson codifies bodies as culturally constructed signs which can be re-signified and transformed. The strategies she adopts to remodel the body reveal a narrative itinerary that goes from the assertion of the lesbian body of the protagonist in Oranges Are Not the Only Fruit to the virtual bodies of the interactive world in The PowerBook. Crossing Boundaries investigates the way in which Winterson works out new bodily paradigms to subvert the effects of social power mechanisms and to dismantle the constructedness of sexual categories and gender differences. In re-mapping bodily boundaries, she also proves that there are almost unlimited possibilities to (de)construct patterns of identity and to remould reality as complex and many-sided.